Sweetest Day of the Year?
by King-Mac-11
Summary: It's Hearts and Hooves Day. Grimoire is single. Grimoire goes to Sugar Cube Corner. Bon Bon finds out Grimoire is single. She decides to play matchmaker for the stallion. This can only end well, right? A Valentine's / Hearts and Hooves Day special. I'm not putting the final decision in the tag section to avoid spoilers.
1. A Bit Much, Don't You Think?

**King: A Valentine's special for Grimoire. I couldn't help it. Had the idea in my head for a while.**

/\

Heart's and Hooves Day. For some, it is the most important holiday to spend with a special somepony. For others, a chance to meet said special somepony. For Grimoire, it was…

 _What day is today? Tuesday?_ Grimoire woke with a loud yawn. The dark grey, red maned unicorn grabbed his notebook, his quill, and his bag before opening his cottage door. He made no secret that he did not enjoy mornings, but he fought through it for his experiments. After he locked his door, he stretched and started his daily walk to Sugar Cube Corner for a breakfast pastry. When he arrived, he waited in an unusually long line before finally making his way to the counter. "Hello. My usual, please."

Mrs. Cake was in charge of the counter today and moved a to-go bag toward the unicorn. "Had it ready for you."

"Thanks, Mrs. Cake."

As he levitated the bag, Mrs. Cake gave him a saccharine smile. "No problem. Thanks for your continued business and Happy Hearts and Hooves Day."

"Huh? Oh… yeah. Sure."

As he walked out, one of the patrons caught Grimoire's statement and it peaked her interest. She thought to herself for a moment before attempting to catch up with the Dark Mage. "Hey!"

Grimoire turned to find a cream coated pony with a cotton-candy-esc mane style. "Um… Hi. Can I help you?"

"Considering the circumstances, I might be able to help you instead. I'm Bon Bon."

"Okay… Nice to meet you. How would you _help_ me exactly?"

"For one thing, it's Heart's and Hooves Day and you are alone."

"Pardon?"

"Don't pretend. I heard that back in Sugar Cube Corner. It's clear you don't have a special somepony and that you're still too new in town to go around to look for one here."

"How could you come to that conclusion based on four words?"

"Please, I'm a professional. I've made a name as a great matchmaker here in Ponyville. So, if you're interested, I could help you find somepony special just for you. I know you're the introverted type and might need a little push for this kind of stuff."

"You can't be serious… You really believe you could find me a special somepony?"

"I don't promise true love. That's up to you. I only promise a pony with the potential."

Grimoire raised an eyebrow. He wanted to argue the issue, but it was clear this pony wouldn't drop the issue. "Fine. You know what, go nuts. If you can find somepony like that, more power to you. If not, no harm no foul." Grimoire wasn't about to get wrapped up in whatever this mare was up to. He left for home and a new experiment. _Besides, I haven't been in town very long. She'll give this up once she realizes she has nowhere to start._

\/

If Grimoire had known that Bon Bon was actually special agent Sweetie Drops, who had extensive files on all the ponies from Ponyville to Canterlot, he might have tried to stop her. Bon Bon trotted to her home and opened the door to her study. After an hour of research, she found… nothing. Grimoire's file ended during his time at the Magic Academy. Thankfully, she had been observing the Dark Mage since his arrival to make sure he wasn't a threat. She knew he was the type that kept to a schedule for some things (like his daily trips to Sugar Cube Corner), but left a lot of time for whatever he wanted to do at the time. He was nice pony, but never got close o most ponies. He likes messing with ponies with his mind. He's the type that enjoys real conversation and genuine debates. This wasn't too difficult. However, his use of Dark magic is an important note to remember as well… If she was going to find somepony for him, they needed to be able to tolerate the Dark magic, if nothing else.

After some time looking over the files, Bon Bon heard a knock on her door. "Hey, Bon Bon!" A familiar mint green pony opened the door and made her way inside without vocal permission.

Bon Bon just rolled her eyes and smiled, "Lyra... I'm a little busy right now."

"Playing matchmaker again?"

"You know I always take this seriously."

"Yeah, I know." Lyra smiled and sat down next to Bon Bon. "So, who's the lucky pony that gets your expertise this year?" Bon Bon slid a file over to Lyra. "Grimoire Maleficarum? Really? He asked for your help with matchmaking?"

"Not quite. I offered and he said he wouldn't stop me."

"Oh… You're taking this as a challenge, aren't you?"

"Naturally. Now, are you going to help me or not?"

"Alright, I'm in. What do you need e to do?"

"I've divided the files into piles. I separated them first to make my life easier."

Lyra looked down onto the table and found said piles. "Um… why are there three of them?"

"One is for the ponies that are taken and the other two are possible piles. I didn't know how he swung, as it were. So, I wanted to cover my bases. After some research, I found out he is straight. So, we only need to focus on the right most pile. I need you to list off the names and I'll think them over."

"Alright."

"Also!" Bon Bon grabbed Lyra's attention before they began, "I need you to speak your mind about any ponies you know. I need all the information I can get to really work."

"Got it!"

"Alright, start us off!"

"Rainbow Dash."

"Hmm… No. Rainbow strikes me as the type to like the hard working, but laid back type."

"Like Sorin?"

"Who?"

"One of her teammates on the Wonderbolts."

"Really?" Bon Bon smiled. "Good to know. I'll keep that for later. Next!"

"Fluttershy."

"I get the feeling Grimoire would scare her more than anything."

"But she's friends with Discord. So, would she really be scared?"

"It's Fluttershy."

"Good point… Next is… Rarity."

Bon Bon raised a hoof toward Lyra. "No! I'm not going anywhere near that sequined can of gem studded worms."

"What's wrong with Rarity?"

"You mean Miss 'I'll find my true prince charming and we'll live in a castle as I design the greatest clothing lines'? It's best not to set her up…"

Lyra felt a sweat drop, "Right…"

Bon Bon sighed. "Alright, Next?"

"Pinkie Pie."

"Maybe…"

"Are you seriously thinking about this one? It's Pinkie Pie."

"I know. She's smart enough that she could offer Grimoire some intellectual stimulation if not genuine curiosity to try to understand her… But her personality might be too over bearing… Okay, never mind. Next?"

"Apple Jack."

"Hard working, driven, though maybe a little too stubborn. I don't see Grimoire settling down to help around an apple farm… Next?"

"Starlight Glimmer."

"I can't see it. Starlight might have something with Sunburst. Next."

"Trixie Lulamoon."

Bon Bon's face turned sour. "I'm not sure she capable of love for any pony but herself. Next."

"Octavia Melody?"

"Why the question?"

"I thought she had a thing with DJ-Pon3…"

"You mean Vinyl Scratch? Nah. They live together and can get along; but, if they actually dated, they'd drive each other insane."

"Alright. Well, they're the next two."

"Octavia might fill the intellectual side… And Vinyl could fill the adventurous experimenter side… Move them both to 'maybe' for now and I'll put some thought into it. Who's next?"

"Spitfire."

"Captain of the Wonderbolts… outgoing but disciplined… add her to 'maybe.' Next?"

"Moon Dancer… I'd suggest we skip her."

"Why?"

"She just got out of her shell and is getting used to friends again. This might be a little too much for her."

"Alright. Then who's next?"

After an hour of listing off ponies, the 'maybe's increased by two. Considering the list spanned every available mare in Equestria, that wasn't necessarily a good thing. There should have been at least a few more… Lyra flipped the last page with her magic and sighed. "That's it."

"Alright… I'll look them over and…"

"Hey, Bon Bon?"

"What's up?"

"Why weren't Twilight, Luna, and Celestia on the list? They're eligible mares, aren't they?"

"Yeah… but Royalty is a subject I want to avoid with this. They have enough on their plates as it is."

"I guess… but Cadence didn't seem overwhelmed with Shining Armor. And Grimoire seems like the type that would help them if he could…"

"There is the Dark magic issue as well. Celestia would find it too dangerous, for now. Luna might be able to look passed it, but she's too much of a mystery for me to be certain. As for Twilight… that's its own oddity that I'd rather not deal with."

"So… just add Luna."

Bon Bon sighed. "Alright. I'll add her to the list when look the files over. Thanks for your help."

"Any time."

\/

As the sun began to set on the horizon, Grimoire made his way home from dropping off his report to Twilight. The night always calmed him. It felt more real for some reason. Didn't really matter, though. He was going to head home and enjoy a good book. Granted, he was in no hurry to arrive. The night just felt so nice, he found himself singing.

 ** _Stepping out into the Darkness, in a world far below. Hold fast your determination, through the ice and the snow. Something creeping up behind you, wonder where did they go? Hold fast your determination… are they friend, are they foe?_**

He was interrupted when Bon Bon jumped out onto the road, "Grimoire!"

The pony jumped so high and was so startled he took his alicorn form and clung to a cloud. When he looked down toward the ground, he saw who had scared him. "Don't do that! You nearly gave me a heart attack!"

"Sorry… could you come down here so we can talk."

Grimoire let go of the cloud and floated back down to the ground. "What?"

"Well… I've been looking for possible matches for you since this morning."

"Don't you have your own somepony? Kind of eating away time, don't you think?"

"My life choices are mine to make. Anyway, I think I might know the mare for you."

"I doubt that. But please, by all means, show your work."

"Well, I thought about it and narrowed the choices down through stages. And I think I might be on to something."

"Aright. Your findings?"

"That's just it…"

"This should be good."

"At first I thought maybe Spitfire, from the Wonderbolts. But she might be too driven by her job, so that doesn't really work out. Then I thought, maybe Rose Luck, but then I remembered that she might be a little overly dramatic…"

"She puts Rarity to shame."

"Right… Anyway, then either Octavia or Vinyl. I know you like music. Though I'm not sure about the personalities…"

"Are you going somewhere with this?"

"Yes! So be quiet until I'm done."

"Alright. Continue."

"Then Lyra thought I should think about Luna."

"Princess Luna?"

"The same. But it didn't work. Then I decided to think Twilight over for the list but…"

"Best not…"

"Right."

"And?"

"Like I said, I might know the pony for you. The problem is, I wasn't sure. Until now."

"Pardon?"

"You're not the only one that read faces, Grimoire. Your date is set up for right now!"

"My what?!"

Grimoire didn't have time to protest as Bon Bon dragged him off to Ponyville Park. When they arrived, Grimoire (who had not reverted back to unicorn form, mind you) took control of his situation and hovered over Bon Bon.

"Look, I let you do what you wanted because I thought it wouldn't get back to me. I knew you wouldn't find a mare for me because I'm looking for a special somepony. I'm perfectly content with my life."

"I know. But it can't hurt, right?"

"It could…" His voice was not worried. It was threatening. He was holding himself back.

"How about you give it a chance. I went through all this trouble…"

Grimoire sighed and returned to the ground, returning to his unicorn form. "Fine. Let's get this over with."

"Awesome!" Bon Bon smiled. "Your date should be here soon. But, a word of warning… don't expect her to talk too much."

"I can live with that…"

Grimoire was forced to sit at a medium sized picnic blanket. There were a few items on the blanket: some cupcakes, some punch, and two glasses. As he waited, he couldn't help but wonder who she had decided on. Whatever she saw in his face had to have been confusion at best. He didn't really know any ponies in town and he only recognized a couple names from her list (Luna, Twilight, and he at least heard of Spitfire). The others were a little beyond him.

He started to get irritated as time passed and gave serious thought about leaving. _This is ridiculous…_

"Ahem…" Bon Bon cleared her throat to get Grimoire's attention. "Allow me the honor of introductions. Grimoire Maleficarum, this is Vinyl. Vinyl Scratch, meet Grimoire."

The white unicorn mare kept bobbing her head to the music in her headphones, giving no indication that she had heard Bon Bon. Her two-toned blue mane was a mess, but it was the kind of messy that looked deliberate. Grimoire had to admit that she was attractive, but he wouldn't go any further just yet.

He stood up and raised his hoof toward her, "Nice to meet you."

She just kept bobbing her head.

Bon Bon laughed nervously. "Okay… I'll leave you two to it…" She backed away slowly as if to distance herself incase things don't work out. Her reputation was on the line though…

Grimoire sighed and shook his head. "Look, I don't know what Bon Bon's up to; but, if you want, we can just walk away and pretend this never happened."

Vinyl removed her headphones and trotted over to the blanket. Taking a seat, she gestured for him to sit as well.

"Alright…" When he sat down, he turned to her, "Mute?"

She nodded.

"Hmm… Expression through music?"

She nodded again.

Grimoire smiled. "Cool. What genre?"

She levitated her headphones toward him, placing them on his ears. After a moment, she took them back.

"Dance music… It suits you."

Vinyl raised an eyebrow.

"Difficult to get right or understand, but a beautiful sound when you can."

Vinyl smiled and let out a small laugh.

The 'date' went off without a hitch, as far as Bon Bon could tell. True, Grimoire and Vinyl didn't walk away like the stereotypical couple… but they didn't storm off in a fit either. They were at least friends. Bon Bon walked over to Grimoire. "Well?"

He let out a defeated sigh. "Okay… credit where's credit's due. I like her."

"Then you're…?"

"Don't get ahead of yourself. I'm not against her. We're friends… I think."

"You think?"

"I've been traveling in exile for most of life to this point. Not a lot of time for friends, much less a relationship, so this is all new ground. You've done your job. Whatever happens next is up to us."

"Awesome!"

"But I warn you…" His smiled never faded, "Don't push anything. Understand? Our pace, not yours."

"G-got it…"

/\

 **King: The song this time is "Turn Around and Shake My Hand" part of Man on the Internet's Undertale the Musical series.**


	2. The Real Sweetest Day Ever!

**King: I bet you thought it was over, didn't you? Ha! This is the real "Sweetest Day". Everyone always talks about Valentine's or Hearts and Hooves Day like it's so very important. No one ever talks about what happens after. Well, here's the after.**

 **/\**

Bon Bon trotted through town with a smile. It was a beautiful day and it was starting to look like it will be a beautiful night soon. She took in the scenes as ponies around her were talking, enjoying each other's company, or just basking in the daylight. As she walked, she found a scene that brought a smile to her face. Grimoire and Vinyl were sitting at a café table. To some, this would be nothing impressive. But, just three days after their meeting, they were already on another date? That was excellent news to the matchmaker.

However, after a second glance, she saw that the scene was a little different. Between them wasn't a pair of pastries nor a shared shake. Resting on the table between them was a large blueprint. Vinyl was watching Grimoire and Grimoire was scanning the floor plan.

Bon Bon had to know what was going on, so she trotted up. "Hey you two! What's going on?"

Grimoire looked up from the paper. "Hey Bon Bon." He returned his eyes to the paper, but continued, "Vinyl asked me to look over the floor plan for her new club in Canterlot."

Bon Bon looked over to the DJ, "You own a club in Canterlot?"

"She's Co-owner, apparently. Just bought an old club and wants to make sure it's ready for operation." He never took his eyes off the plan, "Vinyl," after the DJ turned her head back toward Grimoire he continued without looking up, "If this is the current plan, I see an issue." He marked a series of locations. "The electrical system running the lights in the floor are old and inefficient. This would eat your profits in electrical expenses. I'd suggest that you get that fixed. Granted, it would keep the club out of operation for a while…"

Vinyl's expression turned a little sour before giving a reluctant sigh and nodding.

"Okay. There should be plenty of contractors in Canterlot. Shouldn't take more than a few days. However, there is also some structural issues you'll need to deal with before opening. Minor things, shouldn't be terribly difficult to fix. I've marked them as I've seen them. It would be best to get this reviewed by a professional."

Vinyl nodded and took the print and placed it in her saddlebag. Once their business was done, she hopped down from her chair and trotted off toward the train station.

Bon Bon watched her trot away for a moment before returning her attention to Grimoire. "So… this wasn't a…"

"No. It wasn't. She asked for my help, so I helped her. Nothing else to it."

"But… I thought you were…"

"You thought wrong. I told you before, we are friends now. That's something, but nothing more."

"Dang… I thought you two had hit it off."

"Doesn't matter." He dropped down to the ground.

Bon Bon sighed. "Alright… Is there any possibility that she might be your special somepony?"

"Doubt it. Then again, I won't know unless it happens."

"Huh…" Before Grimoire could trot away, Bon Bon draped one of forelegs around his shoulders. "Alright. I have failed you as a matchmaker. So, now I'm going to make it up to you."

"What?"

"I made a guarantee that I would find you a pony with the potential to be the special somepony. Though you two became friends, I have failed in my task. So, I have to make it up to you."

"No. No you don't."

"Too bad! I'm a professional, I made a guarantee, and I failed. Now I have to pay up!"

"I thought you sold candy, or something…"

"Not the point. Meet me at the train station in one hour!" With that, she rushed off.

Grimoire just shook his head, "This can't end well…"

\/

An hour later, he did arrive at the train station out of a sort of morbid curiosity. Waiting for him was a smiling Bon Bon with a pair of train tickets. She gave him one and rushed him onto the train. After around half an hour, they stepped off onto the Canterlot streets. Grimoire was dragged around town for ten minutes before the Dark Mage lost his patience for the situation.

"Okay, stop." He pulled back and finally stopped Bon Bon's rush. "Where, exactly, are you going with this?"

Bon Bon trotted up to a board and waved toward it, "Tada!"

The sign read, [Theories of Magic in the Three Types of Ponies. A seminar with guest speaker Grimoire Maleficarum.] As Grimoire took in the sign, he turned to Bon Bon, a look of disbelief on his face. "What? How did…"

"I have connections. Now, your lesson beings at 6:30. So, get your stuff together for it."

"Let me get this straight… You, through a series of connections, were able to set up a seminar, get it approved, and get a room dedicated to the lecture in around an hour?"

"It helps when the newest Equestrian princess is living in Ponyville and was a top student in the academy. Knock 'em dead!"

As she trotted away, Grimoire was left to his own thoughts.

\/

Grimoire sat at the front of the room in silence. He watched as ponies entered the room and took their seats. Most of the seats were filled with fifteen minutes before the seminar started. He could tell most of the ponies were students. Some of the ponies in the audience were teachers, some of which he recognized. Whether they recognized him as the expelled Dark Mage, he couldn't tell. Well, he could, but that would require using Dark magic to break into their mind; and he wasn't going to use Dark magic for something so petty.

That said, he certainly thought about it. This was a new feeling for him. He was nervous. Anxious. It was his first chance to teach so many ponies at once. This was his dream; and now that he had it, he was starting to have his share of doubts. His history made it difficult to expect them to take his words at face value. The Dark magic thing doesn't help when speaking to anypony in Canterlot, after all… He took a deep breath and looked over to the clock. 6:20. He wanted a way to diffuse the situation in his mind.

A thought went back to his time in the academy and one of his professors. "Okay!" He stood up and cracked his neck while he spoke, "Now, I know it's still a little early. But I would like to welcome you all to this seminar. Now, I would like to ask, how many of you have had Professor Bronze Hoof?" As a series of hooves were raised, Grimoire noticed that the very teacher he referencing was in the seats. Grimoire had to keep his focus, though. "Okay. Well, for those of you that never had the good professor, here's the deal. If anypony walks through that door after we start, I want all of you to stop whatever you're doing and stare in their direction until they take a seat."

One of the ponies in the seats raised her hoof.

Grimoire smiled, "We haven't started yet. You don't have to raise your hoof."

"Oh… well, I wanted to ask why we would have to stare."

"Simple. This is a lecture and somepony showing up late can be distracting. The stares of an entire room will often lead to some embarrassment for the pony in question, leading to increased punctuality to avoid the feeling."

"And… if they just stand there to run the clock?"

"Then they'll be robbing you of valuable learning." The clock ticked forward again. 6:30. "Alright. Let's get started."

\/

After an hour and a half, the lecture ended and the ponies started to leave the room. A few stayed behind to ask general questions about the material. Some welcomed Grimoire to the campus. One happened to be Professor Bronze Hoof.

The professor trotted up and smiled. "It's nice to see my teaching style has made an impact."

Grimoire smiled. "Yeah… well, it should work with the current students just as well as my year."

"So, how have you been doing since the academy?"

"Um… fine. I guess."

"Oh? So your expulsion didn't affect you too badly?"

"You… you remember that?"

"Kind of hard to forget your star student getting expelled for using Dark magic."

Grimoire chuckled nervously.

"I've been meaning to ask if I ever got the chance…"

 _Here it comes. The 'why would you ever go near Dark magic?'_ Grimoire had been used to that question from his self-imposed exile.

"Why did you leave?"

Grimoire blinked in disbelief. "What?"

"Why did you leave Canterlot? You didn't have to. So, I'd like to know why."

"Oh… Um… Sorry, I'm not used to answering that one… I guess, I left because I didn't have a reason to stay. I wanted to learn as much I could, and I wasn't going to be able to do that in Canterlot anymore."

Professor Bronze Hoof smiled. "I guess that's an acceptable reason."

"Huh… I'm not used to ponies being able to get passed the whole Dark magic thing…"

"Yeah, well… there'll likely be more than a few ponies so stuck up their own butts that they won't. Anyway, it was nice seeing you again." With that, the professor trotted off.

Grimoire, having answered all the ponies' questions, walked back toward the train station. _Today was the best day ever!_


End file.
